N. D. Arote et al. / Tetrahedron Letters 48 (2007) 3651–3653
3653
HO
O
O
Rappoport, Z., Ed.; Wiley-Intersience: New York, 1970;
(c) North, M. In Comprehensive Organic Functional Group
Transformation; Katritzky, A. R., Meth-Cohn, O., Rees,
C. W., Eds.; Pergamon: Oxford, 1995; p 617.
I
OH
I
O
NH3
O
RCHO
+
RCH=NH
R-CN
3. (a) Wang, E. C.; Lin, G. J. Tetrahedron Lett. 1998, 39,
4047; (b) Miller, C. P.; Kaufman, D. H. Synlett 2000,
1169; (c) Das, B.; Ramesh, C.; Madhusudhan, P. Synlett
2000, 1599.
O
Scheme 2. A plausible reaction pathway.
4. Nishiyama, K.; Oba, M.; Watanabe, A. Tetrahedron 1987,
43, 693.
5. Elmorsy, S. S.; El-Ahl, A.-A. S.; Soliman, H.; Amer, F. A.
Tetrahedron Lett. 1995, 36, 2639.
obtained from the reduction of IBX has been recycled
by oxidation.10
6. Suziki, H.; Nakaya, C. Synthesis 1992, 641.
In summary, a simple, chemoselective, efficient and mild
method has been developed for direct conversion of
aldehydes into nitriles.
7. (a) Brackman, W.; Smit, P. J. Recl. Trev. Chim. 1963, 82,
757; (b) Parameswaram, K. N.; Friedman, O. M. Chem.
Ind. (London) 1965, 988; (c) Misono, A.; Osa, T.; Koda, S.
Bull. Chem. Soc. Jpn. 1966, 39, 854; (d) Sato, R.; Itoh, Y.;
Itep, K.; Nihina, H.; Goto, T.; Saito, M. Chem. Lett. 1984,
1913; (e) Erman, M. B.; Snow, J. W.; Williams, M. J.
Tetrahedron Lett. 2000, 41, 6749; (f) Talukdar, S.; Hsu, J.
L.; Chou, T. C.; Fang, J. M. Tetrahedron Lett. 2001, 42,
1103; (g) Bandgar, B. P.; Makone, S. S. Synth. Commun.
2006, 36, 1347.
Acknowledgement
The authors wish to thank the Council of Scientific and
Industrial Research (CSIR), New Delhi, India, for
financial support.
8. (a) Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. J.
Org. Chem. 2003, 68, 5422; (b) Shukla, V. G.; Salgaonkar,
P. D.; Akamanchi, K. G. Synlett 2005, 9, 1483; (c)
Bhalerao, D. S.; Mahajan, U. S.; Chaudhari, K. H.;
Akamanchi, K. G. J. Org. Chem. 2007, 72, 662.
9. Aldehyde (5 mmol) was added to a stirred solution of IBX
(7.5 mmol) in aqueous ammonia (20 ml of a 28–30%
solution, Sp. gravity = 0.89) and acetonitrile (3 ml) at
room temperature. The resultant clear solution became
turbid as the reaction proceeded. After completion of the
reaction as indicated by TLC, the reaction mixture was
diluted with water and extracted with ethyl acetate
(2 · 25 ml). The combined organic layer was washed
successively with water (2 · 25 ml), and brine (25 ml),
dried over sodium sulfate and concentrated under vacuo
to afford practically pure nitrile.
Supplementary data
Spectral data for the compounds in Table 1 can be
found, in the online version. Supplementary data associ-
ated with this article can be found, in the online version,
References and notes
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